Hotels with Pool & Resorts in Westchester from AU$139

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Check availability on Westchester Hotels with Pool

Our top choices for Westchester hotels with a pool

Indoor pool, open 7:00 AM to 10:00 PM, pool loungers

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile
3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (3,098 reviews)
"Great location and friendly staff. "
United States
Pablo
The price is AU$149
includes taxes & fees
25 Feb - 26 Feb
Aloft Chicago Mag Mile
Indoor pool

The Wade

The Wade
4.5 star property
Downtown Chicago
8.4 out of 10, Very good, (1,683 reviews)
"Lovely room, beautiful hotel, wonderful staff, ideal location to navy pier & Michigan Ave. "
United States
Norah
The price is AU$148
includes taxes & fees
22 Feb - 23 Feb
The Wade
Indoor pool

Palmer House a Hilton Hotel

Palmer House a Hilton Hotel
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2,301 reviews)
"Excellent stay, we loved it "
United States
Melani
The price is AU$286
includes taxes & fees
7 Mar - 8 Mar
Palmer House a Hilton Hotel
Indoor pool

Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,083 reviews)
"Amazing location, excellent service and great pool and hot tub. "
United States
Tim
The price is AU$252
includes taxes & fees
24 Feb - 25 Feb
Hyatt Centric Chicago Magnificent Mile
Indoor pool, pool loungers

Renaissance Chicago Downtown Hotel

Renaissance Chicago Downtown Hotel
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,006 reviews)
"Wonderful location and staff was top notch."
United States
M Kim
The price is AU$346
includes taxes & fees
6 Mar - 7 Mar
Renaissance Chicago Downtown Hotel
Outdoor pool, pool cabanas (surcharge), pool umbrellas

DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (2,321 reviews)
"Great staff, room spotless, great price."
United States
Robert
The price is AU$162
includes taxes & fees
26 Feb - 27 Feb
DoubleTree by Hilton Chicago - Magnificent Mile
Seasonal outdoor pool

The Hoxton Chicago

The Hoxton Chicago
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,004 reviews)
"Amazing, I loved my stay"
United States
Valerie
The Hoxton Chicago
Fitness facility

Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (1,599 reviews)
"We had a great stay! Everything was great!"
United States
Megan
The price is AU$330
includes taxes & fees
22 Feb - 23 Feb
Sheraton Grand Chicago Riverwalk
Seasonal outdoor pool

Level Chicago - River North

Level Chicago - River North
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (848 reviews)
"Great stay. Would come again. "
United States
Gracie
Level Chicago - River North
Pool

Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop
3.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (1,858 reviews)
"Absolutely enjoyed my time here"
United States
Quayshaun
The price is AU$139
includes taxes & fees
24 Feb - 25 Feb
Hilton Garden Inn Chicago Downtown South Loop
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Choose what matters most at hotels with a pool in Westchester

Breakfast included
Spa pool

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Top Westchester Hotel Reviews

Hilton Chicago

Hilton Chicago

10/10 Excellent
"Staff was courteous and our lake view room was great. Kids enjoyed the pool. "
Lashaila 1-night trip
Posted 1 day ago
Hilton Chicago

Frequently asked questions

What are some accommodation options with pools in Westchester?
Congress Plaza Hotel: Hotel, 4-minute walk from Michigan Avenue. Provides full, an indoor pool and flat-screen televisions. Hilton Chicago O'Hare Airport: Hotel, 4-minute walk from State Street. Features 2 restaurants, an indoor pool and a health club. Embassy Suites by Hilton Chicago Downtown River North: Hotel, 3-minute walk from Michigan Avenue. Features a snack bar/deli, an indoor pool and complimentary wireless Internet access. Hilton Chicago: Hotel, 2-minute walk from Michigan Avenue. Offers an indoor pool and flat-screen televisions. Hotel Riu Plaza Chicago: Hotel, 5-minute walk from Michigan Avenue. Provides a rooftop terrace, a seasonal outdoor pool and LED televisions.
What is there to see and do in Westchester?
While you're in the area, consider exploring places such as United Center, Wrigley Field and Michigan Avenue. Take a walk along the waterfront at Oak Street Beach and North Avenue Beach. The restaurants and shopping are just some of the things to enjoy while you're in the area.
When is the best time to book a hotel with a pool in Westchester?
You may want to consider a place to stay that has an outdoor pool if you plan to visit Westchester in the hottest months of July, August or June, when the average temp is 22°C. Accommodation with an indoor pool may be the way to go if you come to town during the coldest months of January, February or December, when the average temp is -1°C.